Dress To Impress – Your Guide To A Good Looking Suit

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Dress To Impress – Your Guide To A Good Looking Suit

Working in an office in downtown Chicago day after day gives me a lot of time to people watch, especially if I’m grabbing a coffee in the lobby or having lunch at The Metropolitan Club on the 67th floor of the Willis (not a big deal but kind of a big deal). I see all sorts of suits. Expensive, shabby, fashion forward, etcetera and so on. I like the classic look on a certain person. A guy in his 40s or 50s doesn’t need to be wearing a slim fit suit. The tailoring that was popular in the 80s or 90s with this generation is a good look for them, but we need to keep it with them. That means a few things for any of you 20-somethings looking to cop a new suit.

I’m by no means a fashion expert, but if you follow these rules you’re more than likely looking good — or, at the very least, not having people look at you sideways and saying to themselves, “Wow, that guy dresses like a fucking idiot.” I’m not saying you need to stop shopping for all of your suit needs at Jos A. Bank, but I am telling you to go to a third party tailor. The guys who do tailoring at Jos A. Banks will have you wearing baggy pants and a jacket that’s two sizes too big because they’re perennially stuck in the 90s and that’s how they think suits should fit.


A good pair of dress shoes is going to run you somewhere between 150-300 dollars. Anything above $300, I’m not touching. But if you have the means, go for it. Double monks are in right now, as are dress boots like the Chelsea. Loafers like the penny and tassel never go out of style either. In my opinion, the only no-no when it comes to shoes are the square toe. There are Instagram accounts dedicated to this atrocity of a shoe. The square-toed dress shoe is the Crocs gardening slip-on of the business world. If you’re wearing a square toe, you probably still wear those shiny, faux silk dress shirts and need someone else to tie your tie for you.


A big thing I’ve noticed is a shift away from full suits. More and more I see people wearing a blazer with a different colored pant. Love this look. There are so many more options when you’re not hampered by one solid color. But buying pants off the rack usually does not work. You need to find a tailor who will, at the very least, bring the waist in for you. Apparently belt-less is a look that people are doing now. I’m not into it, but it does look pretty clean when you’ve got the right outfit on. Stay away from pleated pants, and make the sure the break on them is slightly above the shoe. Show off a little sock, or if you’re going loafers just go with the no-show sock.


The biggest rule for jackets is knowing your shoulder width. You don’t want to buy a sports jacket or a full suit that makes you look twenty pounds heavier than you actually are because the jacket is too big. Just don’t buy shit off the rack and expect to wear it out of the store. Spend an extra 80 dollars and get everything tailored. The cheapest suit in the world can look great with proper tailoring. The second biggest rule is to keep it to three buttons and under. This isn’t the 2001 NBA Draft. You’re not allowed to wear a jacket with four buttons on it. You’ll just end up looking like that picture of 17-year-old you in a rental tux at prom. Nobody knew what the fuck they were doing at 17 walking into a tux shop. We all looked like fools. I think three buttons is even pushing it, but if you’re really tall you can pull that look off. Two buttons is obviously the most common, followed by one if you’re wearing a tuxedo jacket. Tough to pull off the tuxedo jacket, but if you can do it without looking like a waiter, I promise you that it’s fire.


I love to see people wearing ties incorrectly. One of my favorites is looking at pictures of people on Facebook who never wear dress clothes and think they look super fly at some wedding they went to. One look at the tie that doesn’t go past their belly button and it’s instant laughter for me. Even worse than that is the guy who doesn’t own a sports jacket. Just showing up to formal events wearing a tie and some khakis like he’s going to the middle school winter ball. I should also mention that novelty ties, like a tie with smiley faces all over it or rubber duckies are a HUGE red flag. Just, please don’t do it. And never, under any circumstances go with a quadruple Windsor knot like Merrill Hodge on Sportscenter. Leave that tie knot for retired middle linebackers.


It’s all about the collar, baby. Oxford, tab, spread, they’re all great. Just make sure the shirt fits. You don’t want to swimming in it, and as I said before leave the silk shirts for Latin nightclub owners and douchebags who frequent said nightclubs. Oh, and do not forget your collar stays.

Image via Shutterstock

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